ZA201701723B - Methods of separating gemcitabine-phosphate diastereoisomers - Google Patents
Methods of separating gemcitabine-phosphate diastereoisomersInfo
- Publication number
- ZA201701723B ZA201701723B ZA2017/01723A ZA201701723A ZA201701723B ZA 201701723 B ZA201701723 B ZA 201701723B ZA 2017/01723 A ZA2017/01723 A ZA 2017/01723A ZA 201701723 A ZA201701723 A ZA 201701723A ZA 201701723 B ZA201701723 B ZA 201701723B
- Authority
- ZA
- South Africa
- Prior art keywords
- gemcitabine
- phosphate
- separating
- methods
- alaninyl
- Prior art date
Links
- 229910019142 PO4 Inorganic materials 0.000 title abstract 5
- 239000010452 phosphate Substances 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 3
- 238000002425 crystallisation Methods 0.000 abstract 2
- NHTKGYOMICWFQZ-BBOXMAMFSA-N fosgemcitabine palabenamide Chemical compound C[C@H](N[P@](=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)C(F)(F)[C@@H]1O)OC1=CC=CC=C1)C(=O)OCC1=CC=CC=C1 NHTKGYOMICWFQZ-BBOXMAMFSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
This application relates to a method of separating the phosphate diastereoisomers of gemcitabine-[phenyl-benzoxy-L-alaninyl)]-phosphate (NUC-1031) using crystallisation. In particular, crystallisation from isopropyl alcohol provides gemcitabine-[phenyl-benzoxy-L-alaninyl)]-(S)-phosphate in high diastereoisomerically pure form. This application also relates to a crystalline form of gemcitabine-[phenyl-benzoxy-L-alaninyl)]-(S)-phosphate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1417644.0A GB201417644D0 (en) | 2014-10-06 | 2014-10-06 | Method of separating phosphate diastereoisomers |
| PCT/GB2015/052839 WO2016055769A1 (en) | 2014-10-06 | 2015-09-29 | Methods of separating gemcitabine-phosphate diastereoisomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA201701723B true ZA201701723B (en) | 2023-11-29 |
Family
ID=51946917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA2017/01723A ZA201701723B (en) | 2014-10-06 | 2017-03-09 | Methods of separating gemcitabine-phosphate diastereoisomers |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US10669300B2 (en) |
| EP (2) | EP3204398B1 (en) |
| JP (2) | JP6893172B2 (en) |
| KR (1) | KR102532498B1 (en) |
| CN (2) | CN112552362A (en) |
| AU (2) | AU2015329767B2 (en) |
| CA (1) | CA2959977C (en) |
| CL (1) | CL2017000819A1 (en) |
| CY (1) | CY1123061T1 (en) |
| DK (1) | DK3204398T3 (en) |
| EA (1) | EA033118B1 (en) |
| ES (1) | ES2793957T3 (en) |
| GB (1) | GB201417644D0 (en) |
| HR (1) | HRP20200849T1 (en) |
| HU (1) | HUE050882T2 (en) |
| IL (1) | IL251125B (en) |
| LT (1) | LT3204398T (en) |
| MA (1) | MA41039B1 (en) |
| ME (1) | ME03730B (en) |
| MX (2) | MX373944B (en) |
| MY (1) | MY183302A (en) |
| PH (1) | PH12017500586A1 (en) |
| PL (1) | PL3204398T3 (en) |
| PT (1) | PT3204398T (en) |
| RS (1) | RS60634B1 (en) |
| SG (2) | SG11201701885UA (en) |
| SI (1) | SI3204398T1 (en) |
| SM (1) | SMT202000410T1 (en) |
| WO (1) | WO2016055769A1 (en) |
| ZA (1) | ZA201701723B (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0317009D0 (en) * | 2003-07-21 | 2003-08-27 | Univ Cardiff | Chemical compounds |
| ES2627195T3 (en) | 2012-11-16 | 2017-07-27 | University College Cardiff Consultants Limited | Mixture of RP / SP gemcitabine- [phenyl- (bencloxy-l-alaninyl)] - phosphate |
| DK3119794T3 (en) | 2014-06-25 | 2018-01-22 | NuCana plc | FORMULA CONTAINING A GEMCITABIN PRODRUG |
| WO2015198058A1 (en) | 2014-06-25 | 2015-12-30 | Nucana Biomed Limited | Gemcitabine prodrugs |
| GB201417644D0 (en) | 2014-10-06 | 2014-11-19 | Nucana Biomed Ltd | Method of separating phosphate diastereoisomers |
| CN106543252A (en) | 2015-09-16 | 2017-03-29 | 博瑞生物医药（苏州）股份有限公司 | The Preparation Method And Their Intermediate of nucleoside phosphoramidate class prodrug |
| CN106543220A (en) | 2015-09-16 | 2017-03-29 | 博瑞生物医药（苏州）股份有限公司 | Phosphoramidate compounds and preparation method thereof and crystal |
| CN106478753A (en) | 2015-09-16 | 2017-03-08 | 博瑞生物医药（苏州）股份有限公司 | A kind of preparation method of NUC 1031 individual isomer and purposes |
| EA037248B1 (en) | 2015-10-05 | 2021-02-26 | НУКАНА ПиЭлСи | Use of gemcitabine[phenyl-benzoxy-l-alaninyl]phophate in combination with carboplatin |
| WO2017098252A1 (en) | 2015-12-11 | 2017-06-15 | Nucana Biomed Limited | Diastereoselective synthesis of phosphate derivatives and of the gemcitabine prodrug nuc-1031 |
| GB201522771D0 (en) * | 2015-12-23 | 2016-02-03 | Nucana Biomed Ltd | Crystalline form of a phosphate derivative |
| WO2018019188A1 (en) * | 2016-07-23 | 2018-02-01 | 博瑞生物医药（苏州）股份有限公司 | Polymorph of nucleoside phosphoramidate prodrug and preparation method therefor |
| GB201709471D0 (en) | 2017-06-14 | 2017-07-26 | Nucana Biomed Ltd | Diastereoselective synthesis of hosphate derivatives |
| CN107400156B (en) * | 2017-09-19 | 2020-01-31 | 北京大学 | A kind of method for separating ergostane-type triterpene 25R- and 25S-epimer |
| CN115028594A (en) * | 2020-06-03 | 2022-09-09 | 吴卫东 | Emotitabine medicinal precursor compound and preparation method and medical application thereof |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001058835A1 (en) * | 2000-02-11 | 2001-08-16 | Degussa Ag | Resolution of dl-racemic mixtures |
| GB0317009D0 (en) | 2003-07-21 | 2003-08-27 | Univ Cardiff | Chemical compounds |
| FR2954310B1 (en) * | 2009-12-18 | 2014-07-25 | Univ Rouen | METHOD FOR DEDOLDING ENANTIOMERS BY PREFERENTIAL EVAPOCRYSTALLIZATION |
| ES2627195T3 (en) | 2012-11-16 | 2017-07-27 | University College Cardiff Consultants Limited | Mixture of RP / SP gemcitabine- [phenyl- (bencloxy-l-alaninyl)] - phosphate |
| WO2014204856A1 (en) | 2013-06-17 | 2014-12-24 | Catabasis Pharmaceuticals, Inc. | Fatty acid anticancer derivatives and their uses |
| KR20160099090A (en) * | 2013-11-27 | 2016-08-19 | 아이데닉스 파마슈티칼스 엘엘씨 | Nucleotides for the treatment of liver cancer |
| DK3119794T3 (en) * | 2014-06-25 | 2018-01-22 | NuCana plc | FORMULA CONTAINING A GEMCITABIN PRODRUG |
| WO2015198058A1 (en) | 2014-06-25 | 2015-12-30 | Nucana Biomed Limited | Gemcitabine prodrugs |
| CN106795198B (en) | 2014-07-22 | 2019-09-06 | 努卡那公共有限公司 | Process for the preparation of gemcitabine-[phenyl(benzyloxy-L-alanyl)]phosphate |
| GB201417644D0 (en) | 2014-10-06 | 2014-11-19 | Nucana Biomed Ltd | Method of separating phosphate diastereoisomers |
| MX390506B (en) | 2015-05-14 | 2025-03-20 | NuCana plc | NUC-1031 (GEMCITABINE-[PHENYL-BENZOXY-L-ALANINYL])-PHOSPHATE) FOR USE IN NEOADJUVANT AND ADJUVANT TREATMENT IN PATIENTS WITH CANCER. |
| EA037248B1 (en) | 2015-10-05 | 2021-02-26 | НУКАНА ПиЭлСи | Use of gemcitabine[phenyl-benzoxy-l-alaninyl]phophate in combination with carboplatin |
| WO2017098252A1 (en) | 2015-12-11 | 2017-06-15 | Nucana Biomed Limited | Diastereoselective synthesis of phosphate derivatives and of the gemcitabine prodrug nuc-1031 |
| AU2015418015B2 (en) | 2015-12-23 | 2021-12-09 | NuCana plc | Combination therapy |
| ES2778933T3 (en) | 2015-12-23 | 2020-08-12 | NuCana plc | Combination therapy |
| GB201522771D0 (en) | 2015-12-23 | 2016-02-03 | Nucana Biomed Ltd | Crystalline form of a phosphate derivative |
-
2014
- 2014-10-06 GB GBGB1417644.0A patent/GB201417644D0/en not_active Ceased
-
2015
- 2015-09-29 PL PL15782005T patent/PL3204398T3/en unknown
- 2015-09-29 DK DK15782005.1T patent/DK3204398T3/en active
- 2015-09-29 ES ES15782005T patent/ES2793957T3/en active Active
- 2015-09-29 LT LTEP15782005.1T patent/LT3204398T/en unknown
- 2015-09-29 WO PCT/GB2015/052839 patent/WO2016055769A1/en not_active Ceased
- 2015-09-29 ME MEP-2020-104A patent/ME03730B/en unknown
- 2015-09-29 SG SG11201701885UA patent/SG11201701885UA/en unknown
- 2015-09-29 HR HRP20200849TT patent/HRP20200849T1/en unknown
- 2015-09-29 EP EP15782005.1A patent/EP3204398B1/en active Active
- 2015-09-29 US US15/514,673 patent/US10669300B2/en active Active
- 2015-09-29 MY MYPI2017000434A patent/MY183302A/en unknown
- 2015-09-29 KR KR1020177012012A patent/KR102532498B1/en active Active
- 2015-09-29 EA EA201790794A patent/EA033118B1/en unknown
- 2015-09-29 RS RS20200611A patent/RS60634B1/en unknown
- 2015-09-29 CA CA2959977A patent/CA2959977C/en active Active
- 2015-09-29 JP JP2017518474A patent/JP6893172B2/en not_active Expired - Fee Related
- 2015-09-29 HU HUE15782005A patent/HUE050882T2/en unknown
- 2015-09-29 EP EP20172701.3A patent/EP3725794A1/en not_active Withdrawn
- 2015-09-29 SG SG10201902952SA patent/SG10201902952SA/en unknown
- 2015-09-29 AU AU2015329767A patent/AU2015329767B2/en not_active Ceased
- 2015-09-29 MX MX2017004446A patent/MX373944B/en active IP Right Grant
- 2015-09-29 PT PT157820051T patent/PT3204398T/en unknown
- 2015-09-29 SI SI201531226T patent/SI3204398T1/en unknown
- 2015-09-29 MA MA41039A patent/MA41039B1/en unknown
- 2015-09-29 CN CN202011494200.9A patent/CN112552362A/en active Pending
- 2015-09-29 SM SM20200410T patent/SMT202000410T1/en unknown
- 2015-09-29 MX MX2020003758A patent/MX387346B/en unknown
- 2015-09-29 CN CN201580054225.8A patent/CN107108682B/en not_active Expired - Fee Related
-
2017
- 2017-03-09 ZA ZA2017/01723A patent/ZA201701723B/en unknown
- 2017-03-13 IL IL251125A patent/IL251125B/en active IP Right Grant
- 2017-03-30 PH PH12017500586A patent/PH12017500586A1/en unknown
- 2017-04-04 CL CL2017000819A patent/CL2017000819A1/en unknown
-
2020
- 2020-04-23 JP JP2020076624A patent/JP6967625B2/en not_active Expired - Fee Related
- 2020-05-25 CY CY20201100477T patent/CY1123061T1/en unknown
- 2020-06-05 AU AU2020203714A patent/AU2020203714B2/en not_active Ceased
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